Risk Management

March 2026

• Mar 5, 2026ConceptsWhat Is Decision Making Under Uncertainty?Frank Knight separated risk, where probabilities are known, from uncertainty, where they cannot be meaningfully assigned, and most big decisions sit on the second side. This guide maps four levels of knowability, then covers satisficing, reversible bets, scenario planning and Bayesian updating. Tetlock's Expert Political Judgment study, spanning about 20 years and more than 28,000 forecasts from 284 experts, found most specialists predicted little better than chance.32 MIN28.0k
• Mar 3, 2026ConceptsRisk vs Uncertainty: What People ConfuseFrank Knight's 1921 line between known probabilities and genuine uncertainty, mapped across a five-step spectrum from casino games to questions no distribution covers. The page explains why optimization gives way to robustness, optionality and heuristics once probabilities stop being meaningful, and uses LTCM's roughly $4.6 billion loss in 1998, the Challenger launch decision and COVID-19 preparedness to show what happens when uncertainty gets dressed up as calculable risk.24 MIN65.4k

December 2025

• Dec 25, 2025TechnologySecurity Risk Management: Assessing and Mitigating RisksMaersk had already identified its outdated, unpatched systems and formally accepted the risk, judging a major cyberattack unlikely. In June 2017 NotPetya spread across 49,000 laptops in seven minutes and halted operations at 76 terminals, with recovery estimated at $300 million. This guide walks through asset identification, threat modeling with STRIDE and MITRE ATT&CK, quantitative FAIR analysis, and the four response strategies, mitigate, accept, transfer, avoid.28 MIN32.7k

October 2025

• Oct 9, 2025Work SkillsCommon Reasons Projects Fail: Understanding PitfallsThe Sydney Opera House remains the archetype, approved in 1957 against a four-year timeline and an estimate near 3.5 million, then finished 14 years later at roughly 49 million because the sail roofs had not been engineered when the project was approved. Engineering proceeded alongside construction, forcing constant redesign. His fix is reference class forecasting, anchoring estimates to how comparable past projects actually turned out rather than to bottom-up optimism.19 MIN49.8k
• Oct 7, 2025Work SkillsEffective Strategies for Project Risk ManagementHis book The Failure of Risk Management argues that the most widely adopted qualitative scoring does not outperform unstructured expert judgment, which matters given how universal those matrices are. The practical alternative here is grounding probability in history rather than intuition, since if the last three comparable integrations slipped then integration delay is likely whatever the team believes this time. It also covers the pre-mortem and assumption analysis.16 MIN15.0k

August 2025

• Aug 12, 2025IdeasLow-Risk Learning ProjectsThe case against the dramatic career leap. Adam Grant's Originals cites research by Raffiee and Feng finding that entrepreneurs who kept their day jobs were 33 percent less likely to fail than those who quit. The same logic applies to skill building: separate risk into its financial, career, time and reversibility dimensions, then design projects you can exit at any stage. Internal work, private builds, informational interviews and open source all qualify.21 MIN7.7k

July 2025

• Jul 7, 2025ExplainersRisk Assessment TemplateMitchell, Russo and Pennington found that prospective hindsight, imagining an outcome has already happened, raised people's ability to name reasons for it by 30 percent over ordinary forward-looking thinking, which is why Gary Klein's pre-mortem works. The template covers seven risk categories, 1-5 probability and impact scales, the risk matrix and its limits, the four responses of avoid, reduce, transfer and accept, plus key risk indicators.28 MIN70.7k

June 2025

• Jun 13, 2025ExplainersHow to Conduct a Premortem: Identify Project RisksVeinott, Klein and Wiggins had 178 participants evaluate a pandemic response plan, and the premortem roughly doubled the debiasing effect of pro and con analysis while leaving reported commitment to execution intact. That answers the usual objection that dwelling on failure demoralizes a team. The gain traces to prospective hindsight, which Mitchell, Russo and Pennington found produces more specific and actionable explanations, not merely more of them.53 MIN64.4k

June 2022

• Jun 29, 2022ConceptsFinancial Risk Management Failures: The Cobra Effect in FinancePortfolio insurance sold index futures automatically as prices fell. On October 19, 1987 that logic ran at scale, the Dow lost 22.6 percent in one session, and the Brady Commission named the strategy a significant contributing factor. The pattern repeats: Long-Term Capital Management, advised by two Nobel laureates and levered roughly 25 to 1, lost 4.6 billion dollars in four months once correlations its models treated as independent moved together.18 MIN5.1k